In Over Our Heads
by LazilyPsychotic
Summary: Bootlegger AU: The Resistance is a rum-running gang based out of Maz's Cantina when a new gang, the First Order, moves into town and starts taking over their supply chain. Luckily the resistance has a plucky new member that they can send undercover as a lounge singer at the Finalizer Cafe to figure out the movements of the First order's shipments. Reylo, Rey/Hux


**Hey everyone! Yes I am alive and kicking. The other stories of mine should be updated soon! I got the idea from this from the lovely Tumblr blog orange-lightsaber, so if you're on Tumblr, check it out! This is also going to be simultaniously updated on AO3. I love all of my lovely readers, and I hope to be able to satisfy this new fandom that I love as dearly as the rest. So without further ado, I present to you In Over Our Heads!**

 **Disclaimer: Don't own any of the Star Wars movies, nor do I own the characters.**

 **Love you all!**

 **LP**

* * *

 **Chapter 1**

"Boss? We have the report for you on the rum barrel count from Cuba."

Leia Organa looked up from her desk, her wispy hair had worked itself out of the bun at the back of her head and was now curling in front of her aging, yet still delicate, face, just in time to see her small and wiry assistant walk toward her with a leather-bound book from her husband's latest run. He placed it in front of her.

"This thing is so water-logged that you can't even make out what it says!" She huffed in exasperation.

"Y-yes about that, Captain Solo's schooner has disappeared. This and a few barrels were all that we could find in the place where he was supposed to rendezvous with the appointed land carriers."

Leia pursed her lips and opened the soggy book, wondering why she had to deal with her husband's foolishness.

A sigh could be heard throughout the basement operation under Maz's Cantina in Boston.

"We have more work cut out for us than I realized. Call in the Scavenger. See if she can salvage what's left of this."

Her assistant, Colum, nodded and left in a hurry to ring up their number one newbie, the Scavenger.

His fingers shook as he rolled the dial on the telephone. He drew the microphone from the holder on the side of the speaker, and pulled the speaker to his ear.

"H-hello, operator? I need you to connect me to 1362 Common Street, apartment number 7." His tenor voice wavered, but grew stronger, knowing that if the rookie heard his voice like that when she answered that he would never hear the end of it and waited for her to pick up on her end on the line.

The line picked up. "You have reached the residence of Rey Kenobi, entertainer and lounge singer. How may I help you?" Came out her tired and dead voice. She must have been working late last night.

"Good afternoon Miss Rey. I have an offer for a new job at Maz's Cantina on Anne Street. I presume you know where the establishment is located." Colum said in a stable and controlled manner. They both knew that these lines were not secure, so any true information had to be shared face to face at the cantina.

"What time should I be there?" Came her mildly intrigued reply. She kept her words steady though.

"In two hours. Not a minute later." He placed the microphone back in its holder and placed the contraption on the counter, ending the conversation.

Rey moved back to her medium sized bedroom, and sat on the boudoir chair that was next to her window. She stared at her reflection, as she opened up one of her boxes holding her headpieces. She pulled out a three string pearl head band that was designed to clip on the sides of her head, and leave strands of pearls on either sides of her ears. Jewels were encrusted onto the clips that attached to her hair. Feathers were placed on either side of the metal headband that was to be placed underneath stylized hair. From what she had been told at the orphanage where she was raised, it had been her mother's. A gift of sorts from a

She placed the headpiece on the boudoir, and stood up. Over by the window, she saw a small blue jay flitting about. Standing up, she walked over to the wardrobe, and opened the doors.

There were so many outfits and costumes for her various jobs that they barely fit inside the wooden box.

Rey rummaged around before her hand grazed over a beige winter dress that would be perfect for walking around Boston at this time of day.

The dress was fitted in the normal fashion, and loosened around mid-thigh. A darker brown bordered along the fitted part of the dress. The border turned into points in the front and back of the dress, and small delicate tassels hung from the points. It gave the whole appearance a tunic and skirt look. The top was sleeveless, but had a sheer wrap that attached to the material at her shoulder. The dress was a high neck, and the over-all look was quite elegant.

Rey put the under garments, stockings and dress on, then moved over to the mirror. She smiled softly, and pulled her hair back into a tight chignon. She smoothed her skirt and went to grab the matching pair of beige heels.

At the door she grabbed a fashionable winter hat and her fur-lined coat from her coat rack. The coat came past her knees to mid-calf.

Rey exited her room and walked into the foyer. She checked herself in the small mirror on the wall next to her, to make sure she was presentable, and left her flat in search of a taxi.

The sky was very bleak and grey, which did not bode well for Rey's new job. She could just tell.

She finally hailed a taxi and the driver helped her into the large black machine.

When Rey reached the cantina, Colum was waiting for her inside.

"Good afternoon, Miss Rey. I believe your day has gone well, yes?" the man inquired as he removed her coat for her. She took off her hat and placed it on the rack next to her coat.

"Quite well, thank you. What was this job you were telling me about Colum?" she asked, her eyebrow raised in question.

"Ah, well, the boss wants to talk to you about it personally."

Colum began to lead her downstairs, when the door opened and a blur of tan, leathery skin, and clothing rushed in. Maz.

"Hurry! Hide Rey! You can't be seen here. The competition has just decided to send word of a visit today. Go up to the attic. If they see you, we won't be able to use you to against them, and you're the best there is." The little woman hurriedly told Rey.

Colum pushed Rey towards the back stairwell, and she hurried up the steps, making sure to crouch low as she moved so that no one can see her. She reached the latch to the attic and pushed her way through.

To one side there is a small hole that Rey can peer through, and she crawled her way through the dark attic over there.

Rey stopped and placed her eye to see through to the lower level right into the front of the cantina. She saw Maz remove Rey's coat and hat, and hide them.

Right then the door opened and men in white suits with black vests, shirts and ties walk in. They even have matching hats that they all seemed to take off simultaneously. Then, as if they couldn't look even more like big shots, a very imposing man who had to be over six feet walked in. He refused to remove his black hat that covered most of his face from Rey's vantage point.

"Kylo Ren, to what do we owe the pleasure of your visit here?" Maz asked, ever the diplomat.

"Hello Maz. It's a pleasure to finally meet you after all of this time. The First Order sends its regards towards you." His voice was a rich baritone and it captivated Rey's attention.

"Cut to the chase." Maz huffed out, and crosseds her arms over her chest.

"We just wanted to stop by and say hello to our new business rival." The man, Kylo, said, and shrugged his shoulders.

"Well, since you've done that, would you be so kind as to leave this establishment?" Came Maz's heated reply.

"Of course, and if you need anything, we have just moved in a few streets over." Rey can hear the evident sarcasm that laced his voice, as he handed Maz a business card. The spell his voice had had on her broke instantaneously, and she felt the beginning traces of dislike run through her.

"I doubt I'll need anything, but thank you for the… generous offer." Maz spat back.

"Say hello to your boss for me." His laugh carried through to the attic. It was an eerie, almost mechanical laugh one might associate with those who don't have feelings.

As they left, Rey could see beautiful black curls forming around the collar of his immaculately tailored suit jacket and shirt.

She waited until she heard Maz starting to ascend the stairs to fetch her, then left the attic.

"What was that about Maz? Who is that guy and how do you know hi-" Rey whispered

"Shush!" Maz pointed toward the door and Rey saw that a slight shadow was still there. After a moment, it left.

"He's a part of the rival bootlegging gang, the First Order. In fact he is the head of their security group. They call them the Knights of Ren. Pah. We need Luke Skywalker back to start up our own security again. It hasn't been the same since the Jedi team was destroyed by none other than Kylo Ren." She stopped, and looked at Rey.

"He used to be one of us you know. I can't tell you more, but maybe the boss might. Go on down and tell her everything that happened." Maz shooed Rey away with her hands.

Rey just smiled, and walked over to the basement door in the corner of the room, and opened it. She climbed down and moved through the hallway to the room that held the boss of the enter Resistance Bootlegging Corp. herself. Leia Solo-Organa.

She knocked on the door.

"General Organa?" Rey called.

"Come in." Came the tired voice of the middle aged woman.

Rey walked in to see the normally organized room in a state of mild chaos.

"I have news from upstairs. Just a few moments ago, one Kylo Ren and part of the First Order appeared in Maz's cantina. It seemed like they were there only to intimidate though." Rey reported.

Leia had frozen in her seat.

"Who was here?" Her voice was strained and brittle.

"Kylo Ren, ma'am." Rey looked at Leia curiously.

"No… he can't have been here. The last report said he was in New York…" The general's voice whispered more to herself than to Rey.

"If I might ask, who is he?"

"No one of your concern Rey. Just a deserter. Nothing more. You said he was with the group the First Order?"

"Yes, ma'am."

"I have a new job for you then. I need you to infiltrate them as soon as possible, find out why they are really here. We'll send someone else to do the job we had originally planned for you. Post flyers. Make them want you to be their lounge singer. We'll have some reviews posted as well. Oh and Rey? Find out about their supply chain, and if they are snatching our shipments, make them pay!" Leia smiled tensely.

Rey knew that it was useless to pry into the boss' affairs, so she just nodded and left.

When Rey returned home, she got to work on creating a flyer about her work as a lounge singer. When she was satisfied, she removed her day clothes, and put on her warm nightgown and crawled into bed.

o0o

The next day, Rey awoke fairly early, and rummaged through her wardrobe to find a presentable winter dress to go to the printer's and then to walk around Boston in. She finally settled on a dark grey dress that reached her ankles, and grabbed a dark coat. She left fairly early and walked down the street to the printer's shop.

The bell at the door dinged and the old man who owned the business hobbled out. His glasses perched on his nose precariously, and his white shirt already slightly tinged with ink.

"Miss Rey! What a pleasure to see you here today. I thought you were going to take a break from singing for a while." He smiled kindly at her.

"Oh, you know me. I can't sit still for too long." She laughed softly and handed him the design she wished to have printed on the press.

"Ah, this block will be easy to carve out. Come back tomorrow and half of the papers you order shall be done." He pulled the design to him and walked over to the brand new brass cashier.

"That will cost you 57 dollars, Miss Rey, but, seeing as it's you, I'll make it 24 dollars, not a penny more."

"Oh, Mister Grant! You're such a kind soul, but I really must protest as to you dropping the price, yes, 57 dollars is pretty steep for me, but you needn't drop the price for me."

"Non-sense. You just keep up the dream of your career and I'll help you out on the side. Now, 24 dollars please."

Rey opened the small purse that was kept inside her coat, and counted out 24 dollars for old Grant.

"Thank you again Mister Grant!" Rey smiled and left the store.

She then proceeded to walk along the streets of Boston, mapping out where she should place her flyers.

All of a sudden, Rey bumps into something hard,

"Ouch!" She looked up to see a man in a perfectly tailored black suit. His black hair was curling around his face and collar. She definitely recognized the hair, and now she had a face to place it with. His skin was a beautiful white, and his eyes a captivating dark chocolate. His nose, which would make anyone else appear ugly or silly, made him appear slightly aristocratic. There was something very familiar about the way his face was shaped, almost as if she had met a relative of his. She shook her head dismissing the idea.

"E-excuse me…" She stammered out, wanting to appear coy and defenseless.

"Watch where you're going next time. Get your head out of the clouds when you walk around these streets." Came his rough reply.

Rey narrowed her eyes.

"Well, I normally don't have tall men walking in my way on the wrong side of the flow of pedestrians." She points to the way everyone was walking to and fro.

His eyes flared.

"Be quiet and leave."

Rey huffed and walked away.

' _How am I supposed to deal with someone as conceited as him?_ ' she wondered despairingly.

When she finished her scouting, she walked back home. Her feet were terribly sore, but she just ignored it and went to the bathroom to wash up.

She finished bathing herself, and got into bed. Her covers were nice and warm, and she sank into them, tired.

Kylo stormed angrily into the Finalizer café. Hux looked over at him from the other end of the room.

"What has you in such a mood?" The wiry ginger asked him, standing up. He was tall, but not as tall as Kylo. Hux's skin made kylo's look tan.

"It's none of your concern." Kylo replied tersely.

Hux rolled his eyes and sat back down.

Kylo left the main room and walked to the back of the building. He stopped at the stairs leading up to the second floor where all of the reserved occasions were to be held. Looking up, he wondered whether he should go up the third floor and retreat into his room to cool his head.

Realizing that he should, he bounded up the stairs two at a time.

Kylo reached his room in record time and slammed the door. He crossed his Spartan style room and sat on his bed. His mind kept replaying that scene on the sidewalk with that girl he bumped into. He had done it on purpose, to make the girl, who was obviously distracted by her thoughts, flustered. It seemed to have worked for a second, but he could tell he really hadn't flustered her, but the calm way she was standing. It was almost as if she let him bump into her.

The worst blow to him, was how she had assessed the situation and corrected his accusation.

Kylo was captivated when he saw her. There was a certain light that drew him to her. He thought of how beautiful she looked, her hair was a beautiful color of coffee and caramel. Her skin had a beautiful tan to it, almost as if she lived in the sun her entire life.

He growled in frustration, and punched the night stand next to his bed. He shouldn't become attached to any of the locals. She looked like one of those law abiding citizens. The ones who agreed with the law that banned alcohol from the United States.

' _But, she was so beautiful…_ '

His mind kept replaying their meeting until he finally lied down on the bed and closed his eyes, drifting off to sleep.

In the morning Rey followed the same routine as the day before, except this time her dress was a beautiful cream color. She put on the same coat as yesterday, and headed to see Grant.

"Good morning!" She called into the shop as she walked in.

Grant looked up from the wooden desk he was working at and smiled at her.

"I have those flyers I promised you. Come back for the other half this afternoon. I'm almost finished with them."

"Oh thank you so much!"

Rey grabbed the flyers and started to post them up around the area she had bumped into the mysterious Kylo Ren for most of the morning. She then decided to hide and watch some. Sure enough he stopped to look at one of them, and pulled it down. The flyer soon disappeared into his coat, and he stalked off.

Rey smiled to herself and went back to Grant's.

"I finished posting the ones you gave me!" She called out into the shop.

Grant's head poked around the corner.

"Wonderful, dear. I'm finishing up the last of them, so it was perfect timing." His head moved back around the corner, and Rey waited for him to finish up.

He hobbled out with the rest of them and handed them to her.

"Thank you for being so wonderful Grant!" She gave him one of her rare hugs, and left the store, smiling softly. She started to walk around to the other places that she thought would be good, to make it seem like the flyers were everywhere, not just in the one area. As she rounded the corner a familiar black suit bumped into her, scattering the remaining posters.

Rey cried out in despair and began to scramble to pick them up. Kylo did nothing to help.

She stood up and hurried away.

"Wait!" Kylo's voice carried through the air.

Rey froze.

"I want to offer you a job, Klutz."

She looked up into those captivating eyes.

"Y-you do?" She hesitated.

"Yes, the business I work for just opened an establishment, and we are looking for some entertainment. Since yours was the first flyer I've seen, you'll get the job." His eyes were cold, and dark with an emotion Rey couldn't place.

She tried to contain her excitement at how easy it was to infiltrate the First Order.

"Okay…" Rey smiled hesitantly.

"Good, follow me to the café." He stalked off, not bothering to check if Rey was following.

She hurried after him, slightly annoyed at his lack of caring.

Kylo had hardly believed his luck. This morning, he had unconsciously walked to the last place he had seen the girl, and saw her posting flyers for something.

' _So that's what she was doing looking at things yesterday._ '

He had waited for her to leave, and walked over to the flyer closest to him. It read as follows:

' _ **Rey Kenobi**_

 _ **Lounge Singer and Entertainer**_

 _ **Will work at any place of decent reputation, no questions asked.**_

 _ **For more information, send your operator through to 1362 Common Street,**_

 _ **apartment number seven.**_

 _ **I look forward to doing business with you.**_ '

Kylo had shaken his head in disbelief at his luck, and had looked around to search for the girl, but she vanished.

He shrugged his shoulders thinking about how eventful his morning had been, and started to walk to where he was actually supposed to be. Right before he turned the corner onto the street the shop was on, the girl bumped into him. He watched as she froze in shock and recognition, and a brief smirk flitted across his face.

The flyers she was holding flew from her grasp from the impact against him.

He heard her cry out and watched, fascinated, at the speed in which she picked up the flyers. They had stayed miraculously clean and undamaged.

He shook his head to clear it, and was surprised to see her form retreating quickly.

"Wait!" His voice called out before he could stop himself.

He saw the girl stop where she was, almost as if she feared something.

Kylo decided to play it safe and seem emotionally detached.

"I want to offer you a job, Klutz." He added the Klutz at the end to hide the excitement he was feeling.

She looked into his eyes, and time seemed to stop. Her dark eyes were specked with mesmerizing amber and gold. Rings of an almost grey-silver color circled around the cornea of her eyes.

He was broken out of the strange hold her eyes had on him by her wavering voice.

"Y-you do?"

"Yes, the business I work for has just opened up and establishment, and we are looking for some entertainment. Since yours was the first flyer I've seen, you'll get the job." He schooled his face into a mask of indifference, but his mind was already forming how he could get her to fall for him.

Kylo could see the girl's barely contained excitement.

"Okay…" He could sense her hesitation, but she also had a hint of urgency he took as her need for a job.

"Good follow me to the café." He turned and started walking, wanting to hide how elated he was that she accepted the job.

He realized too late that he was walking to fast for her to keep up, and slowed down for her to catch her breath.

"Please don't be so slow in the future. I won't wait for you." His voice came out colder than he intended.

She looked at him, this time the fire was in her eyes again.

"Oh, I'm so sorry that I'm too slow for His Royal Highness, the Ice Prince. I don't normally walk through this part of Boston. It's a bad place for a lady to walk unaccompanied through here." She crossed her arms over her chest.

It was then that he realized that she was walking these streets alone.

"Have you no one to accompany you throughout this city?"

"No, I live alone in my own flat." Her hair was falling out of its severe chignon, and falling in wisps out of her hat. He took the time to assess her attire, and found she was stylishly dressed, almost as if she was a top class entertainer who really didn't need to print flyers for jobs.

"If you can afford that outfit you're sporting, I think you would more than likely be able to afford a male escort throughout the city every now and then." His eyes narrowed.

The girl rolled her eyes.

"I acquired these clothes from several of my jobs throughout my life. I alter them myself to suit the style of the years. Appearances are all that matter in the material world. Oh that's right, you appear to have always been smartly dressed since you were a boy, so you wouldn't know what it would be like to be sneered at when you show up for a job dressed in an outfit that is behind the style of the day." Her eyes burned into his skull.

"You know nothing of my childhood." He smartly turned and started walking towards the Finalizer.

She hurried to catch up to him, and tripped over her heels slightly. She righted herself with the grace of someone who had been dancing their entire lives, and followed him into the brightly lit café.

Rey looked around in wonder as she surveyed the Finalizer.

It was very modern and stylish. The tables were ornate and delicate, perfect for tea and the ladies who would sit there. The walls had state of the art electrical lamps, and the chandelier at the front gave off the impression of high quality business. If she didn't know any better, she would have never had suspected this place of rum running.

She turned to look at the mysterious Kylo. He was quite handsome, she had to give him that, but she hated how cold and indifferent he was to her. It was almost as if he hated her, and that he really didn't want her to work here.

' _It's going to be really hard to infiltrate the First Order if the one person who I need to accept me as one of them hates me._ '

Right then a man walked up to her. He was in a black suit as well, but he had gold adorning his lapels. His hair was the brightest red she had ever seen. His entire demeanor screamed 'I am in charge, and this space will be spotless at all times'. He had the look of a military man.

"Hello Miss…?" His voice held a slight British accent.

"Rey Kenobi sir." Rey smiled at him her most charming smile.

"My cohort seems to have forgotten mention of you. I run this establishment. Are you the new entertainment?" The man looked at her with kind, yet guarded eyes.

"And you are…?"

"Ah, how terribly silly of me. I am Brendol Hux. I assume you've met Kylo?" Rey's eyes widen. She had forgotten that Kylo had never told her his name. She hoped she hadn't said his name earlier.

"I met him yes, but I didn't know his name." She smiled politely at Kylo's frozen figure.

"How rude of him then. We both are the ones who run this organization as assistant CEO's. It is such a please to meet you Rey Kenobi." He raises his arm for her to take it.

"No, the pleasure is all mine." Her mind was whirling as a new plan formulated in her mind.

' _I don't need Kylo after all… I can just convince this Hux character!_ '

Rey grinned inwardly as she accepted Hux's proffered arm.

' _Let the games begin!_ '


End file.
